Short Synthesis of (R)- and (S)-4-Amino-3-Hydroxybutyric Acid (GABOB)

Marcello Tiecco; Lorenzo Testaferri; Andrea Temperini; Raffaella Terlizzi; Luana Bagnoli; Francesca Marini; Claudio Santi

doi:10.1055/s-2005-861783

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Short Synthesis of (R)- and (S)-4-Amino-3-Hydroxybutyric Acid (GABOB)

Marcello Tiecco*, Lorenzo Testaferri, Andrea Temperini, Raffaella Terlizzi, Luana Bagnoli, Francesca Marini, Claudio Santi
Dipartimento di Chimica e Tecnologia del Farmaco, Sezione di Chimica Organica, Università di Perugia, 06123 Perugia, Italy
Fax: +39(075)5855116; e-Mail: tiecco@unipg.it;

Abstract

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Abstract

A simple and stereospecific synthesis of both (R)- and (S)-GABOB has been developed. The synthetic approach involves the conversion, through organoselenium intermediates, of commercially available ethyl (R)- and (S)-4-chloro-3-hydroxybutyrate into a protected 1,2-amino alcohol with retention of the original configuration.

Key words

selenium oxidation - ring closure - amino acids - β-hydroxyselenides - 1,3-oxazolidin-2-ones

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References

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